|Jimmy the Grape (Games)|
Jackie Estacado (Friend)
|Real World information|
- "That fat fucking piece of shit Paulie thinks he can't be touched, right? *Wrong!* Wrong, wrong, wrong *wrong*. He's gonna be touched all right, oh boy is he gonna be touched!"
- – Jimmy "The Grape" to Jackie. [src]
The Darkness Edit
He stays at the subway station most of the time in The Darkness. He was the one who informed Jackie about Paulie's money savings for the Chicago mob, and who told Jackie that Paulie and Eddie Shrote had kidnapped and taken Jenny to St. Mary's Orphanage after they brutally beat him.
Later, after Paulie's assault on Aunt Sarah's house, Jimmy was the one who offered Jackie temporary donship of the Franchetti family. Over the next two years, Jimmy helps Jackie to run the Franchetti family.
The Darkness II Edit
Two years later, Jackie is attacked by unknown assailants while he has dinner in a restaurant. After he returns home, Jimmy informs Jackie that somebody also torched their warehouses down at the docks and two of their guys got killed outside Gino's deli. Jimmy comes to a conclusion that someone is trying to takeover Jackie's business.
He also expresses his relieve, that Jackie is finally using the Darkness again and adds that a waiter recognized one of the guys who came into the restaurant tonight. That guy is Swifty, who Jackie remembers left just before he got attacked. Together with couple of their boys, Jimmy and Jackie travel to a pool hall, where Swifty runs an executive poker games. Before entering the pool hall, Jackie tells Jimmy and his men to stay behind, while he proceeds alone.
After Jackie takes care of Swifty and returns home, Jimmy informs Jackie that while Eddie and Frank were at the local brother called Brimstone Club, they heard from one of the girls, named Camille about the new owners who moved into the top floor. She also reveals, that some weird guy with a limp goes in and out of the place. Although Jimmy isn't sure if they're still there, he believes that it might be worth checking out. Jackie agrees to head out there, but no before Jimmy informs, that Vinnie has a "friend" who works there, who might help him get inside the brothel.
During Brotherhood's assault on Jackie's mansion, Jimmy together with couple of other men, board up in Jackie's office. When Jackie reaches them, Jimmy urges him to rush and save Aunt Sarah who's locked herself in his panic room and which the Brotherhood are trying to break open. Four days later after the Darkness finishes up healing Jackie's wounds received from Bragg, Jimmy expresses his condolence for Aunt Sarah's death and tries unsuccessfully talk Jackie out of going to her funeral.
At the funeral, Jimmy tried to calm Jackie down regarding Aunt Sarah's death by saying that she will be resting alongside the rest of his family and expressed his frustration that Jenny couldn't be buried here too. He also added that he's fully aware of the burden Jackie carries, but before he can compliment his inner strength, Bragg and the Brotherhood forces attack the funeral.
Later after they return to the mansion, Jimmy together with Vinnie suggest Jackie to lay low for a while or at the very least, accompany him to the Hellgate Field. Jackie refuses and goes alone to face the Brotherhood.
His mental hospital reality counterpart (Dr. James) is shown as a strict elderly man who tells Jackie (during the mental hospital realities) that his "delusions" are inspired by mafia fiction. Dr. James tells Jackie that while mafia fiction is entertaining, it is unacceptable for real life.
Jimmy has New York accent, and usually speaks with some eloquence, as befitting his status as an old-school mobster. His old time gangster and thus prefers the old ways the streets were ruled by. Thus he hated those that didn't show respect and were dishonorable.
- In The Darkness II, when talking to Jimmy in Jackie's office, he says "I knew this guy, Vito Somethin'-or-other. Me an' him did some time in the fifties. Boy, could that kid jack a car." This is a reference to the video game Mafia II, another title made by 2K Games, and its protagonist Vito Scaletta. Vinnie in The Darkness 2 is voiced by the same person as Vito, Rick Pasqualone.